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(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl

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(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Basic information

Product Name:
(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
Synonyms:
  • (R)-(+)-BINAP, (R)-(+)-1,1'-Binaphthalene-2,2'-diylbis(diphenylphosphane)
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthalene 97%
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl
  • R(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHALENE
  • (R)-(+)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL
  • (R)-(+)-2,2BIS(DIPHENYLPHOSPHINO)-1,1-BINAPHTHYL
  • (R)-2,2'-BIS(DIPHENYLPHOSPHINO)-1,1'-BINAPHTHYL
  • (R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl,(R)-BINAP
CAS:
76189-55-4
MF:
C44H32P2
MW:
622.69
EINECS:
616-304-7
Product Categories:
  • Asymmetric Synthesis
  • Phosphine Ligands
  • Synthetic Organic Chemistry
  • Adamantanes
  • B (Classes of Boron Compounds)
  • Ligands
  • chiral
  • Chiral Reagents
  • N-Heterocyclic Carbene Ligands
  • Tetrafluoroborates
  • Peptide
  • Chiral Compound
  • BINAP Series
  • Chiral Phosphine
  • Biphenyl derivatives
  • Aromatics
  • Catalyst
Mol File:
76189-55-4.mol
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(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Chemical Properties

Melting point:
283-286 °C(lit.)
alpha 
240 º (c=0.3, toluene)
Boiling point:
724.3±55.0 °C(Predicted)
refractive index 
235 ° (C=0.3, Toluene)
storage temp. 
Inert atmosphere,Room Temperature
solubility 
Benzene (Slightly), Chloroform (Slightly)
form 
Powder
color 
White to cream-white
optical activity
[α]20/D +222°, c = 0.5% in benzene
Water Solubility 
insoluble
Sensitive 
Air Sensitive
Merck 
14,1223
BRN 
4914063
CAS DataBase Reference
76189-55-4(CAS DataBase Reference)
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Safety Information

Hazard Codes 
Xi,Xn
Risk Statements 
36/37/38-20/21/22
Safety Statements 
22-24/25-37/39-26-36
WGK Germany 
3
F 
8-10-23
TSCA 
No
HS Code 
29319090

MSDS

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(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Usage And Synthesis

Reaction

  1. (R)-BINAP or (R)-Tol-BINAP can be combined with dichloro(1,5-cyclooctadiene)ruthenium to form precursors to NOYORI CATALYST SYSTEMS. These systems exhibit very high catalytic activity and enantioselectivity in the hydrogenation of a wide range of substrates. NOYORI CATALYST SYSTEMS have been shown to effect highly enantioselective hydrogenation of functionalized ketones where the substituents are dialkylamino, hydroxy, siloxy, carbonyl, ester, amide or thioester.
  2. Useful ligand in asymmetric Heck processes.
  3. Ligand employed in palladium-catalyzed asymmetric arylation of ketones.
  4. Ligand employed in rhodium-catalyzed 1,4-additions to enones.
  5. Ligand employed in palladium-catalyzed hydroamination of styrene derivatives.
  6. Ligand employed in silver-catalyzed asymmetric Sakuri-Hosomi allylation and Mukaiyama aldol reaction.
  7. Ligand employed in rhodium-catalyzed kinetic resolution of enynes.
  8. Ligand employed in asymmetric rhodium-catalyzed hydroboration of cyclopropenes.
  9. Ligand employed in silver-catalyzed a-hydroxylation of stannyl enol ethers.
  10. Ligand employed in palladium-catalyzed synthesis of chiral allenes.
  11. Ligand for palladium-catalyzed enantioselective hetero Michael addition to form b-amino acid derivatives.
  12. Ligand employed in rhodium-catalyzed asymmetric rearrangement of alkynyl alkenyl carbinols.
  13. Ligand employed in rhodium-catalyzed 1,2-addition of aluminium organyl compounds to cyclic enones.
  14. Ligand employed in iridium-catalyzed transfer hydrogenative allylation of benzylic alcohols.
  15. Ligand employed in rhodium-catalyzed asymmetric C-Si bond formation by conjugate silyl transfer using a Si-B linkage.
  16. Ligand employed in the iridium-catalyzed asymmetric cyclopropane-mediated carbonyl allylation of primary alcohols.
  17. Ligand employed in the nickel-catalyzed asymmetric α-arylation of tetralones.
  18. Ligand employed in the copper-catalyzed asymmetric propargylation of ketones.
  19. Ligand employed in the cobalt-catalyzed asymmetric reductive coupling of alkynes with alkenes.
  20. Ligand employed in the rhodium-catalyzed asymmetric 1,4-addition of arylalanes on trisubstituted enones.
  21. Ruthenium-catalyzed asymmetric hydrocyanation of imines.
  22. Palladium-catalyzed asymmetric intermolecular cyclization.





Chemical Properties

white to light yellow crystal powde

Uses

Chiral ligand for metal mediated asymmetric catalysis.

Uses

Useful ligand for transition metal catalyzed asymmetric reactions, including hydrogenation and disilylation. 2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl and its rhodium and ruthenium derivatives are highly selective homogeneous catalysts used for the reduction of aryl ketones, β-keto esters, and α-amino ketones. They have also been used for asymmetric hydrogenation and hydroformylation of olefins, asymmetric Heck reactions, and asymmetric isomerizations of allyls.
Complex with Ag(I) used to catalyze an asymmetric aldol reaction between alkenyl trichloroacetates and aldehydes. Also used with Ag(I) to catalyze an enantioselective hetero-Diels-Alder reaction of azo compounds.

General Description

(R)-(+)-2,2′-Bis(diphenylphosphino)-1,1′-binaphthalene is an axially dissymmetric bis(triaryl)phosphine ligand for asymmetric reactions.

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl Preparation Products And Raw materials

Raw materials

EtanolEthyl acetateMethanolDichloromethaneN,N-DimethylformamideAzabenzeneTriphenylphosphineTrifluoroacetic anhydrideNickel(II) chloride hexahydrateTriethylenediamine1,2-Bis(diphenylphosphino)ethane(R)-(+)-1,1'-Bi-2-naphtholDiphenylphosphine

Preparation Products

(3S,4R)-4-Acetoxy-3-[(R)-1-(tert-butyldimethylsilyloxy)ethyl]azetidin-2-one

(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthylSupplier

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(R)-(+)-2,2'-Bis(diphenylphosphino)-1,1'-binaphthyl(76189-55-4)Related Product Information